Hotels in Chestertown

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Dec 7 - Dec 8
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Check prices in Chestertown for tonight, Dec 7 - Dec 8
Dec 8 - Dec 9
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Check prices in Chestertown for tomorrow night, Dec 8 - Dec 9

Top Rated Chestertown Hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.64 mi from city center
$102 nightly
The price is $113 total per night
$113 total
Dec 25 - Dec 26
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$72 nightly
The price is $80 total per night
$80 total
Dec 13 - Dec 14
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a vending machine, and a fireplace in the lobby.
Pet friendly
Parking included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$113 nightly
The price is $126 total per night
$126 total
Dec 8 - Dec 9
Total with taxes and fees
Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
Pool
Parking included
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Free Cancellation
Reserve now, pay when you stay
29.11 mi from city center
$92 nightly
The price is $105 total per night
$105 total
Dec 15 - Dec 16
Total with taxes and fees
Guests of Hampton Inn Baltimore/Glen Burnie enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. If you plan to drive, free parking is available. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include coffee/tea in a common area, express check-out, and a banquet hall.
Breakfast included
Pet friendly
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$355 nightly
The price is $417 total per night
$417 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with luggage storage, securing valuables, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.
Pool
Spa
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.95 mi from city center
$178 nightly
The price is $203 total per night
$203 total
Dec 14 - Dec 15
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with concierge services, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$144 nightly
The price is $164 total per night
$164 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, tours or tickets, and luggage storage. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Pet friendly
Free WiFi
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
$89 nightly
The price is $105 total per night
$105 total
Dec 14 - Dec 15
Total with taxes and fees
Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.36 mi from city center
$95 nightly
The price is $110 total per night
$110 total
Dec 21 - Dec 22
Total with taxes and fees
At Hilton Garden Inn Baltimore/White Marsh, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and dry cleaning/laundry. Other amenities at this family-friendly hotel include meeting rooms, a conference center, and a 24-hour business center.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$64 nightly
The price is $74 total per night
$74 total
Dec 16 - Dec 17
Total with taxes and fees
Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with securing valuables and concierge services. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$62 nightly
The price is $69 total per night
$69 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of Quality Inn & Suites Bel Air I-95 Exit 77A have access to free WiFi in public areas. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

3.5 out of 5
6571 Eastern Avenue Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.39 mi from city center
$103 nightly
The price is $121 total per night
$121 total
Dec 28 - Dec 29
Total with taxes and fees
Guests staying at Hampton Inn Baltimore Bayview Campus enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cheap Chestertown hotels options

    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue Chestertown MD
    $64 nightly
    The price is $70 total per night from Dec 24 to Dec 25
    $70 total
    Dec 24 - Dec 25
    Total with taxes and fees
    5/10 (175 reviews)
    Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    150 Scheeler Road Chestertown MD
    $102 nightly
    The price is $113 total per night from Dec 25 to Dec 26
    $113 total
    Dec 25 - Dec 26
    Total with taxes and fees
    8.4/10 Very Good! (858 reviews)

Where should you stay in Chestertown?

What are some of the best hotels to stay with the kids in Chestertown?

Book one of these hotels for you and the kids in Chestertown. Comfort Inn & Suites Chestertown is a hotel offering free parking, free full breakfast, and laundry facilities. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.

What are the best hotels in central Chestertown?

These are some of the most popular hotels in the center of Chestertown:

Historical Society of Kent County Maryland and Chestertown Historic District are a couple of sights to visit in the heart of Chestertown.

Chestertown hotels essential information

Accommodation
1,085 hotels
Lowest Price
$69
Highest Price
$417
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Hampton Inn Baltimore/Glen Burnie, Pendry Baltimore, Annapolis Waterfront Hotel, Autograph Collection, Historic Inns of Annapolis, Best Western Plus Hotel & Conference Center, Hilton Garden Inn Baltimore/White Marsh, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A, Hampton Inn Baltimore Bayview Campus

Recent Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

5/5 Excellent
"The room was great, but the staff is where this place shines. They were great!"
A verified traveler stayed at Hampton Inn Baltimore/Glen Burnie
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie

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